CN109627461B - Polypyrrole nano composite conductive hydrogel and preparation method thereof - Google Patents
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Abstract
The invention belongs to the technical field of hydrogel materials, and discloses a polypyrrole nano composite conductive hydrogel and a preparation method thereof. The method comprises the following steps: a) pyrrole is used as a monomer, dopamine is used as a dopant, and the polypyrrole nano material is prepared through in-situ chemical oxidative polymerization; b) uniformly mixing a polypyrrole nano material, modified gelatin and a photoinitiator in a solvent, and carrying out ultraviolet light initiated polymerization to obtain a polypyrrole nano composite conductive hydrogel; the modified gelatin is obtained by adopting methacrylic anhydride modified gelatin. The polypyrrole nano material is obtained by modifying polypyrrole with dopamine, can be well dispersed in a hydrogel matrix material, and is beneficial to stable existence of the polypyrrole nano material due to the action of hydrogen bonds between hydrogel molecules; the prepared conductive hydrogel has excellent conductive performance and stable chemical properties, and the mechanical property of the hydrogel is improved.
Description
Technical Field
The invention relates to a polypyrrole nano composite conductive hydrogel and a preparation method thereof, belonging to the technical field of biomedical hydrogel materials.
Background
With the rapid development of the field of tissue engineering, hydrogel materials are receiving attention as their specific extracellular matrix-like components. The traditional hydrogel materials can not meet the increasing functional requirements of people, particularly the repair of electric signal sensitive tissues, such as muscle tissues, myocardial tissues and nerves. Therefore, the conductive hydrogel is produced at the same time, combines the characteristics of the hydrogel and the conductive substance, and is expected to be an ideal biomedical material. For example, it has been shown that conductive hydrogels play a major role in promoting the proliferation of neuronal cell adhesion and inducing Nerve regeneration (Xu, D., et al, "Micro-nano-structured Polyaniline Assembled in cellular Matrix Via Interfacial Polymerization for Applications in neural regeneration." Acs Applied Materials & Interfaces 8.27(2016 17090 17097)).
At present, the conductive hydrogel is mainly formed by compounding a body conductive high polymer material and a hydrogel matrix material. However, since the general conductive polymer is a rigid polymer chain, it is insoluble and difficult to process, and thus has disadvantages of non-uniform dispersion and limited performance in hydrogel synthesis. The commonly used methods for synthesizing the conductive polymer layer mainly include electrochemical synthesis, chemical oxidative polymerization, and the like. For example, a conductive polymer layer is deposited on the surface of the hydrogel by an electrochemical method, so that conductive polymers are introduced on a hydrogel substrate to prepare the conductive hydrogel with uniform and stable properties, and the conductive hydrogel is expected to be used for biological interface materials. But the electrochemical preparation method is complex, the reaction conditions are harsh, the requirements on equipment are high, and the prepared conductive hydrogel has defects in the aspect of mechanical properties. The conductive hydrogel prepared by the chemical oxidative polymerization method has relatively simple preparation method and strong operability. However, the poor dispersibility of the general conductive high molecular polymer material can cause the defects of non-uniformity of the prepared conductive hydrogel and unstable electrical properties, and the application of the conductive hydrogel is limited.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention aims to provide a polypyrrole nano composite conductive hydrogel and a preparation method thereof. The method is simple, the conductive material in the prepared conductive hydrogel is uniformly dispersed in the form of the nano material, and the obtained conductive hydrogel not only has good biocompatibility, but also has good mechanical property and conductivity. The nano particles of the invention enhance the mechanical property and the uniformly dispersed conductive nano particles improve the conductivity.
The purpose of the invention is realized by the following technical scheme:
a preparation method of polypyrrole nano-composite conductive hydrogel comprises the following steps:
a) pyrrole is used as a monomer, dopamine is used as a dopant, and the polypyrrole nano material is prepared through in-situ chemical oxidative polymerization;
b) uniformly mixing a polypyrrole nano material, modified gelatin and a photoinitiator in a solvent, and carrying out ultraviolet light initiated polymerization to obtain a polypyrrole nano composite conductive hydrogel;
the modified gelatin is obtained by adopting methacrylic anhydride modified gelatin.
The polypyrrole nano material in the step a) is prepared by the following method:
and in an acid solution, uniformly mixing pyrrole and dopamine hydrochloride, adding an oxidant, reacting under the ice bath condition, centrifuging, and drying to obtain the polypyrrole nano material.
The acid solution is hydrochloric acid; the molar ratio of dopamine hydrochloride to pyrrole is (0.03-0.3): 1, preferably (0.03-0.16): 1; the volume mass ratio of the pyrrole to the oxidant is (120-240) mu L: (0.6-1.4) g; the volume ratio of the pyrrole to the hydrochloric acid is (120-240) mu L: (20-40) mL, wherein the concentration of hydrochloric acid is 1M; the oxidant is ferric trichloride or ferric trichloride hexahydrate; the reaction is carried out under the condition of stirring, and the stirring rotating speed is 500-800 rpm; the reaction time is 6-12 h; the rotating speed of the centrifugation is 6000-10000 rpm, and the drying is freeze drying.
The specific preparation steps of the modified gelatin in the step b) are dissolving the gelatin in phosphate buffer solution, dripping methacrylic anhydride, reacting, dialyzing and freeze-drying to obtain the modified gelatin. The reaction condition is that the reaction is carried out for 2-4 h at 25-60 ℃. The mass-volume ratio of the gelatin to the methacrylic anhydride is (4-7) g: (3-6) mL; the dropping speed of the methacrylic anhydride is 5-10 s/drop; the mass volume ratio of the gelatin to the phosphate buffer solution is (4-7) g: (40-70) mL; the dialysis is carried out in pure water by adopting a dialysis bag with the molecular weight of 12000-14000 at the temperature of 40-50 ℃ for 5-9 days.
The solvent in the step b) is phosphate buffer solution;
the polypyrrole nano material: modified gelatin: the mass ratio of the photoinitiator is (0.3-1): (1-10): (0.5 to 1); the concentration of the polypyrrole nano material in a phosphate buffer solution is (0.3-1) g: 100 mL.
The photoinitiator is Irgacure 2959.
The conditions of the ultraviolet light initiated polymerization in the step b) are as follows: the intensity of the ultraviolet light source is 5-10 mW/cm2The wavelength of light is 300-460 nm, the working distance is 9-15 cm, and the polymerization time is 60-270 s.
The diameter of the polypyrrole nano material is 90-400 nm, and a nanofiber structure is formed; the hydrogel exhibits a continuous three-dimensional porous structure. And due to chemical blending, the conductive nano-fiber reinforced hydrogel substrate has the effect of obtaining the conductive hydrogel with good mechanical property and excellent electrical property
The conductive nanofiber material is obtained by modifying polypyrrole with dopamine, and can be well dispersed in a hydrogel matrix material, and meanwhile, the conductive nanofiber material has a hydrogen bond effect with hydrogel molecules, so that the conductive nanofiber material is beneficial to stable existence; the prepared conductive hydrogel has excellent conductive performance and stable chemical properties.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the polypyrrole nano material prepared by the invention has controllable morphology, excellent electrical property and good dispersibility, can be uniformly dispersed in a hydrogel matrix material, and solves the problem of poor dispersibility of a conductive polymer.
(2) The nano composite conductive hydrogel prepared by the invention has improved mechanical properties by reinforcing the hydrogel base material through the polypyrrole nano fibers, solves the problem of poor mechanical properties of common hydrogels, and expands the application field of the hydrogel.
(3) The polypyrrole composite conductive hydrogel prepared by the invention is doped with polypyrrole to construct a conductive polymer network, so that the electrical property of the hydrogel is improved, and the electrical property of the hydrogel is stable.
(4) The conductive hydrogel composite system prepared by the invention has good material stability and no toxic or side effect, still maintains the characteristics of hydrogel extracellular matrix, has excellent biocompatibility, and is expected to be used in the tissue engineering repair fields of nerve repair, myocardial tissue regeneration and the like.
Drawings
FIG. 1 is a high power scanning electron micrograph of the polypyrrole nano-fiber material of example 1;
FIG. 2 is a scanning electron micrograph of the polypyrrole nanocomposite conductive hydrogel in example 1;
FIG. 3 is a stress-strain plot of the polypyrrole nanocomposite conductive hydrogel prepared in example 2; methacrylic anhydrified gelatin hydrogel refers to hydrogel that is not compounded with polypyrrole nano-materials;
FIG. 4 is a conductivity bar graph of the polypyrrole nanocomposite conductive hydrogel prepared in example 2; methacrylic anhydrified gelatin hydrogel refers to hydrogel that is not composited with polypyrrole nanomaterial;
fig. 5 is a skeletal staining laser confocal picture of BMSC cells of polypyrrole nanofiber composite conductive hydrogel prepared in example 3.
Detailed Description
The present invention will be further described with reference to the following specific examples and drawings, but the embodiments of the present invention are not limited thereto.
Example 1
A preparation method of polypyrrole nano-composite conductive hydrogel comprises the following steps:
(1) stirring and mixing 120 mu l of pyrrole monomer and 20mL of hydrochloric acid solution with the concentration of 1M under the ice bath condition, adding 0.01g of dopamine hydrochloride, and obtaining a mixed solution after the dopamine hydrochloride is completely dissolved; 0.67g FeCl3 6H2Dissolving O in 5mL of 1M hydrochloric acid solution to prepare FeCl3HCl solution; FeCl to be prepared3Slowly adding HCl solution drop by drop into the mixed solution for about 5s, continuously stirring in an ice bath for 6h, centrifuging at 6000r for 3 times, and freeze-drying and storing the obtained black precipitate, namely the polypyrrole nano material;
(2) weighing 4g of gelatin, placing the gelatin into a reagent bottle with a cover, adding 40mL of phosphate buffer solution (pH 7.4, concentration 0.067M), and stirring at 60 ℃ until the gelatin is completely dissolved; adding 3mL of methacrylic anhydride 5 s/drop into the solution dropwise by using a liquid transfer gun, magnetically stirring the solution in a constant-temperature water bath kettle at 50 ℃ for 2 hours, and transferring the solution to a phosphate buffer solution (with the pH value of 7.4 and the concentration of 0.067M) at 50 ℃ to terminate the reaction; putting the solution into dialysis bag (molecular weight is 12000) in pure water of 50 deg.C, dialyzing for 5 days, centrifuging the liquid in the dialysis bag, collecting supernatant, and lyophilizing to obtain methacrylic acid anhydrization gelatin (modified gelatin);
(3) 0.15g of modified gelatin was weighed and dissolved in 3mL of a phosphate buffer solution (pH 7.4, concentration 0.067M), and added0.015g of photoinitiator Irgacure2959 is placed in an oven at 60 ℃ in the dark until being completely dissolved, 0.009g of dopamine modified polypyrrole nano material is weighed and placed in the solution, and ultrasonic dispersion is carried out for 30min to obtain uniform mixed solution; transferring the mixed solution into a mold, wherein the intensity of an ultraviolet light source is 5mW/cm2The wavelength of light is 360nm, the working distance is 9cm, and the polymerization time is 90 s; and demolding to obtain the polypyrrole nano composite conductive hydrogel.
Fig. 1 shows a scanning electron microscope image of the dopamine-modified polypyrrole nanomaterial (i.e., polypyrrole nanomaterial) obtained in this example. As shown in FIG. 1, the polypyrrole nanomaterial has a nanofiber morphology with a diameter of about 90nm, and the morphology is uniform, thus a continuous network structure is presented.
The scanning electron microscope image of the modified gelatin conductive hydrogel sample composited with polypyrrole nanofibers obtained in this example after freeze-drying (i.e., polypyrrole nanocomposite conductive hydrogel) is shown in fig. 2, and as can be seen from fig. 2, the pores of the composite hydrogel after freeze-drying are uniform and continuous, and the nanofibers are uniformly dispersed in the hydrogel framework.
The polypyrrole nano composite conductive hydrogel obtained in the embodiment has a fracture stress at the maximum deformation position of 0.11 MPa; conductivity 4.2 x 10-4S/cm。
Example 2
A preparation method of polypyrrole nano-composite conductive hydrogel comprises the following steps:
(1) taking 180 mu l of pyrrole monomer into a round-bottom flask carrying 30mL of hydrochloric acid solution with the concentration of 1M, stirring under the ice bath condition, weighing 0.03g of dopamine hydrochloride into the flask until the dopamine hydrochloride is completely dissolved; weigh 0.99gFeCl3 6H2Dissolving O in a small beaker filled with 7.5mL of 1M hydrochloric acid solution, and stirring by magnetic force until the O is completely dissolved to prepare FeCl3HCl solution; FeCl to be prepared3Slowly adding HCl solution dropwise into the mixed solution for about 4s, and continuously stirring for 8h under ice bath; transferring the liquid into a centrifugal tube, centrifuging at 7000r of rotation speed for 3 times to obtain black precipitate, namely polypyrrole nano material, and freeze-drying and storing;
(2) weighing 5g of gelatin, placing the gelatin into a reagent bottle with a cover, adding 50mL of phosphate buffer solution (pH 7.4 and concentration 0.067M), and stirring at 55 ℃ until the gelatin is completely dissolved; 5mL of methacrylic anhydride (8 s/drop) is dropwise added into the solution by a liquid transfer gun, magnetically stirred in a constant-temperature water bath at 45 ℃ for 3 hours, and transferred into a phosphate buffer solution (pH 7.4, concentration 0.067M) at 45 ℃ to terminate the reaction; placing the above solution in dialysis bag (molecular weight of 13000) in pure water of 45 deg.C, dialyzing for 7 days, centrifuging the liquid in dialysis bag, collecting supernatant, and lyophilizing to obtain methacrylic acid anhydridized gelatin (modified gelatin);
(3) weighing 0.2g of modified gelatin sample, dissolving the modified gelatin sample in 3mL of phosphate buffer solution (pH 7.4, concentration 0.067M), adding 0.02g of photoinitiator Irgacure2959, placing the modified gelatin sample in an oven at 60 ℃ in a dark place until the modified gelatin sample is completely dissolved, weighing 0.018g of dopamine-modified polypyrrole nano material, placing the dopamine-modified polypyrrole nano material in the solution, and performing ultrasonic dispersion for 35min to obtain a uniform mixed solution; transferring the mixed solution into a mold, wherein the intensity of an ultraviolet light source is 8mW/cm2The wavelength of light is 400nm, the working distance is 10cm, and the polymerization time is 160 s; and demolding to obtain the polypyrrole nano composite conductive hydrogel.
The mechanical property test of the polypyrrole nanocomposite conductive hydrogel obtained in this example is shown in fig. 3. FIG. 3 is a stress-strain plot of the polypyrrole nanocomposite conductive hydrogel prepared in example 2; methacrylic anhydrified gelatin hydrogel (i.e., methacrylic anhydride grafted gelatin hydrogel) refers to a hydrogel that is not composited with polypyrrole nanomaterial. As can be seen from FIG. 3, the fracture stress of the formed polypyrrole nano material reinforced conductive hydrogel at the maximum deformation position reaches 0.12MPa, which is higher than the fracture stress of the methacrylic anhydride grafted gelatin hydrogel at the same deformation position by 0.044MPa, and the mechanical property of the polypyrrole nano material reinforced conductive hydrogel is obviously improved.
The conductivity test of the polypyrrole nanocomposite conductive hydrogel obtained in this example is shown in fig. 4. FIG. 4 is a conductivity bar graph of the polypyrrole nanocomposite conductive hydrogel prepared in example 2; methacrylic anhydrified gelatin hydrogel (i.e., methacrylic anhydride grafted gelatin hydrogel) refers to a hydrogel that is not composited with polypyrrole nanomaterial. From the figure4, compared with pure methacrylic anhydride grafted gelatin hydrogel, the conductivity of the polypyrrole nano composite conductive hydrogel is from 3.7 to 10- 6The S/cm is increased to 5 x 10-4S/cm, the electrical properties of the hydrogel are excellent.
Example 3
A preparation method of polypyrrole nano-composite conductive hydrogel comprises the following steps:
(1) taking 240 mu l of pyrrole monomer into a round-bottom flask loaded with 40mL of hydrochloric acid solution with the concentration of 1M, stirring under the ice bath condition, weighing 0.2g of dopamine hydrochloride into the flask until the dopamine hydrochloride is completely dissolved; weigh 1.34gFeCl3 6H2Dissolving O in a small beaker filled with 10mL of 1M hydrochloric acid solution, and stirring by magnetic force until the O is completely dissolved to prepare FeCl3HCl solution; FeCl to be prepared3Slowly adding HCl solution into the mixed solution drop by drop for about 3s, and continuously stirring for 10 hours under ice bath; transferring the liquid into a centrifugal tube, centrifuging for 3 times at 10000r of rotation speed to obtain black precipitate, namely polypyrrole nano material, and freeze-drying and storing;
(2) weighing 7g of gelatin, placing the gelatin into a reagent bottle with a cover, adding 70mL of phosphate buffer solution (pH 7.4, concentration 0.067M), and stirring at 50 ℃ until the gelatin is completely dissolved; adding 6mL of methacrylic anhydride 10 s/drop into the solution dropwise by using a liquid transfer gun, magnetically stirring the solution in a constant-temperature water bath kettle at 40 ℃ for 4 hours, and transferring the solution to a phosphate buffer solution (with the pH value of 7.4 and the concentration of 0.067M) at 45 ℃ to terminate the reaction; putting the solution into dialysis bag (molecular weight of 14000) in pure water of 40 deg.C, dialyzing for 9 days, centrifuging the liquid in the dialysis bag, collecting supernatant, and lyophilizing to obtain methacrylic acid anhydrified gelatin (modified gelatin);
(3) weighing 0.3g of modified gelatin sample, dissolving the modified gelatin sample in 3mL of phosphate buffer solution (pH 7.4, concentration 0.067M), adding 0.03g of photoinitiator Irgacure2959, placing the modified gelatin sample in an oven at 60 ℃ in a dark place until the modified gelatin sample is completely dissolved, weighing 0.027g of dopamine-modified polypyrrole nano material, placing the dopamine-modified polypyrrole nano material in the solution, and performing ultrasonic dispersion for 40min to obtain a uniform mixed solution; transferring the mixed solution into a mold, wherein the intensity of an ultraviolet light source is 10mW/cm2Light wavelength of 460nm, the working distance is 15cm, and the polymerization time is 270 s; and demolding to obtain the polypyrrole nano composite conductive hydrogel. The polypyrrole nano composite conductive hydrogel obtained in the embodiment has a fracture stress at the maximum deformation position of 0.13 MPa; conductivity 5.2 x 10-4S/cm。
The hydrogel prepared by the embodiment has a continuous three-dimensional porous structure, the nano material is uniformly dispersed on the hydrogel substrate, the mechanical property of the hydrogel is obviously improved, and the hydrogel has excellent electrical properties.
Analyzing the biocompatibility of the polypyrrole nanocomposite conductive hydrogel, the staining pattern of the polypyrrole conductive hydrogel of this example on the cytoskeleton of BMSC cells is shown in fig. 5. Fig. 5 is a skeletal staining laser confocal picture of BMSC of polypyrrole nanofiber composite conductive hydrogel prepared in example 3. As can be seen from fig. 5, the cells spread well on the hydrogel surface, and the conductive hydrogel had a long fusiform shape, and was excellent in biocompatibility.
Claims (6)
1. A preparation method of polypyrrole nano-composite conductive hydrogel is characterized by comprising the following steps: the method comprises the following steps:
a) pyrrole is used as a monomer, dopamine is used as a dopant, and the polypyrrole nano material is prepared through in-situ chemical oxidative polymerization;
b) uniformly mixing a polypyrrole nano material, modified gelatin and a photoinitiator in a solvent, and carrying out ultraviolet light initiated polymerization to obtain a polypyrrole nano composite conductive hydrogel;
the modified gelatin is obtained by adopting methacrylic anhydride modified gelatin;
the polypyrrole nano material in the step a) is prepared by the following method:
in an acid solution, uniformly mixing pyrrole and dopamine hydrochloride, adding an oxidant, reacting under the ice bath condition, centrifuging, and drying to obtain a polypyrrole nano material; the molar ratio of dopamine hydrochloride to pyrrole is (0.03-0.3): 1; the volume mass ratio of the pyrrole to the oxidant is (120-240) mu L: (0.6-1.4) g; the oxidant is ferric trichloride or ferric trichloride hexahydrate; the acid solution is hydrochloric acid; the volume ratio of the pyrrole to the hydrochloric acid is (120-240) mu L: (20-40) mL, wherein the concentration of hydrochloric acid is 1M; the reaction time is 6-12 h;
the polypyrrole nano material in the step b): modified gelatin: the mass ratio of the photoinitiator is (0.3-1): (1-10): (0.5 to 1);
the conditions of the ultraviolet light initiated polymerization in the step b) are as follows: the intensity of the ultraviolet light source is 5-10 mW/cm2The wavelength of light is 300-460 nm, the working distance is 9-15 cm, and the polymerization time is 60-270 s;
the diameter of the polypyrrole nano material is 90-400 nm, and a nanofiber structure is formed;
the polypyrrole nano composite conductive hydrogel is applied to the field of tissue engineering repair.
2. The preparation method of the polypyrrole nanocomposite conductive hydrogel according to claim 1, wherein: the specific preparation steps of the modified gelatin in the step b) are dissolving the gelatin in phosphate buffer solution, dripping methacrylic anhydride, reacting, dialyzing and freeze-drying to obtain the modified gelatin.
3. The preparation method of the polypyrrole nanocomposite conductive hydrogel according to claim 2, wherein: the reaction condition is that the reaction is carried out for 2-4 h at 25-60 ℃;
the mass-volume ratio of the gelatin to the methacrylic anhydride is (4-7) g: (3-6) mL.
4. The preparation method of the polypyrrole nanocomposite conductive hydrogel according to claim 2, wherein: the dropping speed of the methacrylic anhydride is 5-10 s/drop;
the mass volume ratio of the gelatin to the phosphate buffer solution is (4-7) g: (40-70) mL; the dialysis is carried out in pure water by adopting a dialysis bag with the molecular weight of 12000-14000 at the temperature of 40-50 ℃ for 5-9 days.
5. The preparation method of the polypyrrole nanocomposite conductive hydrogel according to claim 1, wherein: the solvent in the step b) is phosphate buffer solution; the concentration of the polypyrrole nano material in a phosphate buffer solution is (0.3-1) g: 100 mL;
the photoinitiator is Irgacure 2959.
6. A polypyrrole nano composite conductive hydrogel obtained by the preparation method of any one of claims 1 to 5.
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